Day Date
Denim on a first date? You betcha. Just make sure to skip the super slim cuts and work in a pretty standout piece, like a bold wrap.
Image: Imaxtree
Day Date
Mother The Hustler Ankle Fray Jeans, $218 at Shopbop
Day Date
Articles of Society Faith Flare Jean, $29.97 at Nordstrom Rack
Day Date
Free People Bandana Printed Kimono, $148 at Free People
Day Date
Kimchi Blue Ruffle Dreams Floral Print Kimono Jacket, $39.99 at Urban Outfitters
Day Date
Looser fits are appropriate when belted and teamed with an oversized sweater. Toss off those heels, slip on some ice skates and you'll be rink-ready.
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Day Date
Express Light Wash Boyfriend Jeans, $88 at Express
Day Date
Acne Studios Boy Indigo Fray Jeans 32", $330 at Opening Ceremony
Day Date
Silence + Noise Easton Turtleneck Sweater, $79 at Urban Outfitters
Day Date
A flirty patterned dress also fits the daytime date bill, especially when topped off by a black leather jacket.
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Day Date
Ecote Split-Neck Mixed Print Midi Dress, $79 at Urban Outfitters
Day Date
Maeve Lilt Swing Dress, $118 at Anthropologie
Day Date
Barney's Originals Cropped Leather Biker Jacket, $138 at ASOS
Day Date
Topshop DOUBLE UP Strappy Sandal, $52 at Topshop
Drinks After Work
Meeting up with that sure-to-be someone special, but don’t have time to change after work? No sweat. Just plan ahead and pick separates that work both at the office and at the bar, like a relaxed striped blouse and coordinating trousers.
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Drinks After Work
MICHAEL Michael Kors Striped Tie-Neck Blouse, $110 at Michael Kors
Drinks After Work
Parallel Lines Relaxed Wrap Front Shirt in Stripe Print, $46 at ASOS
Drinks After Work
Everlane The Slouchy Trouser, $68 at Everlane
Drinks After Work
You can still suit up as long as it doesn't translate as too corporate. Look for slightly exaggerated blazers and complementary pants for a streamlined effect. Add a set of slipper mules for extra kick.
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Drinks After Work
BCBGMaxAzria Arelia A-Line Coat, $268 at BCBGMaxAzria
Drinks After Work
Lafayette 148 New York Menswear Pants, $348 at Neiman Marcus
Drinks After Work
Gucci Princetown Leather Horsebit Mule Slipper Flat, $595 at Neiman Marcus
Drinks After Work
Matching sets don't have to involve a twinning shell and cardigan. Impress your boss and your date by color coordinating a long-sleeve sweater with a statement skirt.
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Drinks After Work
Peter Pilotto Turtle Neck Jumper, $483.77 at Farfetch
Drinks After Work
Peter Pilotto Asymmetrical Crêpe Skirt, $845 at mytheresa.com
Romantic Dinner
The LWD has gotten a reboot, making it a great selection for an intimate dining experience. Take a cue from style star Alicia Vikander and set your sights on one with eye-catching accents, like an attached scarf or cape detail or even lacy embroidery.
Image: Chad Buchanan/GC Images/Getty Images
Romantic Dinner
Misha Collection Evona Caped Silk Midi Dress, $350 at Nordstrom
Romantic Dinner
BCBGMaxAzria Tracie Asymmetric Lace Dress, $124.60 at Bloomingdale's
Romantic Dinner
If stark white is not your color story, you can never go wrong betting on black. Just pick a piece with a bit of texture in the form of crochet or lace inserts.
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Romantic Dinner
Self-Portrait Bell-Sleeved Lace-Insert Dress, $442 at Matches Fashion
Romantic Dinner
Tracy Reese Crochet Lace Scalloped Hem Midi Dress, $398 at Nordstrom
Romantic Dinner
Zoe Saldana rocked a red hot dress recently boasting a tiered skirt. You can even emulate the layered look with a little off-the-shoulder action.
Image: James Devaney/GC Images/Getty Images
Romantic Dinner
Self-Portrait Off Shoulder Ruffle Dress, $510 at Shopbop
Romantic Dinner
Louise et Cie Esperance Pump, $117.95 at Nordstrom
Night on the Town
Zendaya Coleman loves to push the sartorial limits, but she can also deliver a knockout punch by combining a few key basics. Follow her lead by topping off a chic metallic mini with a crisp white dress shirt before you make the most of the nightlife with your new bae.
Image: Michael Wright/WENN.com
Night on the Town
Topshop Neat Pleated Shirt, $70 at Topshop
Night on the Town
Nasty Gal Jerry Metallic Leather Skirt, $108 at Nasty Gal
Night on the Town
ASOS Metallic Asymmetric Layer Mini Skirt, $30 at ASOS
Night on the Town
Floral patterns and off-the-shoulder tops are both still trending, making them ideal for a first date. Give the look an edge with a sleek leather pencil skirt a la Lily Aldridge.
Image: Donato Sardella/Getty Images for Vanity Fair
Night on the Town
Somedays Lovin Sunny May Off The Shoulder Top, $79 at Revolve
Night on the Town
Vintage Havana Floral Off-The-Shoulder Crop Top, $60 at Bloomingdale's
Night on the Town
ASOS Midi Pencil Skirt in Leather, $138 at ASOS
Night on the Town
Satin bomber jackets are a stylish way to jazz up any ensemble. Try pairing a slim-cut version with a coordinating satin skirt for a look that’s simultaneously sexy and comfortable — key for staying out all night.
Image: Imaxtree
Night on the Town
Topshop Satin Bomber Jacket, $95 at Nordstrom
Night on the Town
ASOS Midi Skirt in Satin With Splices, $57 at ASOS
Night on the Town
Love Moschino I Love Superquilted Evening Crossbody Bag, $157.99 at 6pm.com
We all get first date jitters. All that budding excitement about getting to know someone you really like mixed with the sheer terror of making a fool of yourself. While we can’t guarantee you won’t trip or knock a glass of wine over, we can help ease your mind when it comes to your wardrobe. Picking out the perfect first date outfit is a bit of an art form. And even though we live our lives as you do by following the WWOPW (What Would Olivia Palermo Wear) code, for a first date, you don’t want to complicate things by revealing your sartorial prowess too soon. Because, let’s face it, most fellas don’t exactly appreciate avant–garde outfits. Be patient, you can break out your Elizabethan dress inspired by Valentino’s recent haute couture offering a few months in.
To help you out with what to wear on a first date, we’ve gone ahead and hooked you up with some stellar outfit inspiration along with some shopping picks for you to stock up on. Whether you’re planning a Sunday brunch rendezvous or a late night on the town, we’ve got your first date outfit covered. Where you go from there is all up to you.
[ Next: What to Wear for Date Night, According to Astrology ]
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